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This is a list of questions and answers to rake-compiler-dock. You're welcome to add your own questions, when you've found suitable answers.
A: For gem authors primary working on OS-X or Linux, this allows to build ready-to-run binary gems for Windows in a reproducible way, without digging too much into development on Windows. It is also often less fragile to deliver binary gems, because the Windows build environment is not as much standardized as on Linux.
A: Copy certificate and key into the container through the current working directory. Here is an example: https://github.com/ged/ruby-pg/blob/master/Rakefile.cross#L287
A: rake-compiler-dock respects ftp_proxy, http_proxy and https_proxy variables, so that downloads in build scripts usually work. But make sure you're using IP addresses instead of host names, unless the proxy is publicly available to the internet. Use Google search in regards to the proxy configuration of docker or boot2docker (to download the image).
Q: docker version complains about "certificate is valid for 127.0.0.1, 10.0.2.15, not 192.168.59.107"
A: This is probably due to a bug in boot2docker-1.7.0 . Use one of the fixes in #issue-824 .
A: There should be a new VM in Virtualbox called "boot2docker-vm". Try to start the VM within the VirtualBox GUI. This can give an indication, why the VM can not be started. Alternatively you can try to start the VM on the command prompt, and see what happened, like so: "c:\Program Files\Oracle\VirtualBox\VBoxHeadless.exe" -s boot2docker-vm
A: It could disturb boot2docker, if there are some ancient versions of MSYS tools are in the search path. Try boot2docker start -v to get some debug information what fails.
A: rake-compiler-dock can only mount local drives - network drives can not be used as working directory.
A: The project directory couldn't be mounted into the docker container or it is not accessible. This can be due to SELinux permission restrictions. See http://stackoverflow.com/questions/24288616/permission-denied-on-accessing-host-directory-in-docker